Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Ciaran Paul Seath, James W. B. Fyfe, John J. Molloy, Allan J. B. Watson

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDAàBF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.
LanguageEnglish
Number of pages7
JournalSynthesis
Early online date12 Aug 2016
DOIs
Publication statusE-pub ahead of print - 12 Aug 2016

Fingerprint

Oxidation
Benzofurans
Boronic Acids
Boron
Indoles
Hydrolysis
Acids
oxindole

Keywords

  • boron
  • oxidation
  • heterocycles
  • lactams
  • lactones
  • functionalized oxindoles synthesis
  • benzofuranones
  • boronic acid stability
  • oxindole pharmacophore

Cite this

Seath, Ciaran Paul ; Fyfe, James W. B. ; Molloy, John J. ; Watson, Allan J. B. / Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs. In: Synthesis. 2016.
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Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs. / Seath, Ciaran Paul; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.

In: Synthesis, 12.08.2016.

Research output: Contribution to journalArticle

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AU - Seath, Ciaran Paul

AU - Fyfe, James W. B.

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AU - Watson, Allan J. B.

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KW - boron

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KW - functionalized oxindoles synthesis

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